Phenyl isocyanate → HCID 18446693, compound

HRID 1268751Notes

Reaction equation

HRID 1268751 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:28]([NH:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:29])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 17862961HCID 17862961, compound

Product 1

HCID 18446693HCID 18446693, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [5-(2-methyl-4-pyrimidinyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.8 mmol) in N,N-dimethylacetamide (10 mL) was added phenylisocyanate (0.29 mL, 2.7 mmol), and the mixture was stirred at 80° C. for 2 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The resulting crystals were recrystallized from ethyl acetate-hexane to give the title compound (0.55 g, yield 78%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-49b5c06028064f5494012df584a9b960
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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